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Leonard enlisted at Cincinnati, Ohio.[2] His actions as a sergeant at the Little Blue River near Little Blue, Nebraska on May 15, 1870 led to him being awarded the Medal of Honor on June 22, 1870.[2] While searching for stray horses near the river, Leonard and four other soldiers were ambushed by 50 Indians. The men were able to kill three Indians, and wound seven. After repelling the attack, Leonard then escorted two women and a child to the nearest settlement.[2] The other four soldiers (Pvt. Thomas Hubbard, Pvt. Heth Canfield, Pvt. Michael Himmelsback, Pvt. George W. Thompson) also received Medals of Honor.